Jelly Roll Is Sending One of His Grammys to Prison

Jelly Roll just had a historic night at Sunday night’s Grammy Awards, which included winning three awards—including the first-ever award for Best Contemporary Country Album. While other artists might be planning which shelves or rooms to display this newly acquired collection of gold gramophones, the “I Am Not Okay” singer has other plans.

While promoting his new role as a judge on Netflix’s revival of Star Searchon Entertainment Tonight on Wednesday, host Cassie DiLaura congratulated the singer—whose real name is Jason Bradley DeFord—on his triple Grammy win. To which he replied: “It never gets old.”

While the singer’s wife, Bunnie XO, has already claimed that she is commandeering one of the awards, DiLaura asked if he had a plan for where the other two would be going. “I haven’t said this publicly yet, so I’m going to break it with you,” he responded.

“I’m going to obviously keep one at the studio, because that was my dream. And I think I’m going to give the second one to the [Nashville] County Sheriff, Daron Hall, to put at the jail there,” he added. 

Sarah Michelle Gellar, one of his Star Search co-judges, was clearly impressed, adding: “So people know there’s life after.”

Jelly Roll confirmed that the third award would indeed go to Bunnie.

The 41-year-old music sensation took home three for three on his Grammy nominations this year—his first ever after being previously nominated four times. He won the awards for Best Contemporary Christian Music Performance/Song for “Hard Fought Hallelujah,” Best Contemporary Country Album for Beautifully Broken, and Best Country Duo/Group Performance for “Amen.”

Did Jelly Roll Spend Time in Prison?

The Nashville-born artist has been open about his criminal past, and how it has inspired him as a singer. In a 2023 interview with the Grammy Awards website, Jelly Roll shared that his troubles with the law began at age 14—the same age he was baptized.

“The same year that I got baptized, I got arrested, and that started what would be a 10-year cycle of incarceration in and out,” he said.

Later in the interview, he explained that his run-ins with the law remain at the forefront of his mind, because “I'm reminded of it all the time. So I think that what my goal now is while I'm being constantly reminded that I want to remind people that you can change. I tried to buy a house four months ago, and I was turned down because of my felonies. I'm still dealing with it today. 

“I think it's more now about just trying to bring attention to the cause, to have some sort of justice reform,” he continued. “My felonies that are inexpugnable, that I got whenever I was 16 years old. You know, I wasn't thinking like a man that should have that held against it him for the last 20-some years.”

All told, Jelly Roll has stated that he was in and out of jail approximately 40 times on a variety of charges, including shoplifting and drug dealing. His most serious charges were for felony drug possession in 2008 and an aggravated robbery charge when he was just 16 years old, for which he served more than a year in prison.

On December 18, 2025, Tennessee Governor Bill Lee issued a pardon for Jelly Roll. 

“His story is remarkable, and it's a redemptive, powerful story, which is what you look for and what you hope for,” Lee told reporters at the time.